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Getting Around the Gatekeeper: A Guide for Fundraisers

by Joe Garecht

Closed GateWhen it comes to major donor fundraising, nothing is more important than talking directly with your donors and prospects. To successfully solicit major gifts, you must cultivate your donors and build relationships with them, which requires one-on-one conversations.

Generally speaking, major donors tend to be busy people. They are usually engaged in business or philanthropy at a high level, meaning there are many demands on their time and many people trying to get in touch with them. They are also likely to have assistants and others working for them who can make it difficult for you, as a fundraiser, to reach out to the donor for the first time.

We call these assistants “gatekeepers” because they are the ones who open the mail, answer the phones, and, in some cases, screen the email for your major donor prospects. This means that if you want to speak to the donor directly (on the phone, through Zoom, or as part of an in-person meeting), you will need to get through the gatekeeper first.

Getting around the gatekeeper to reach a new donor prospect may be difficult, but it can be done. Here are four strategies you can use to get through to the donor:

#1: Be Persistent

When reaching out to a new major donor prospect for the first time, persistence is key. Many fundraisers give up after making one or two attempts to reach a new donor. This is a huge mistake. I tell my clients they need to try seven or eight times before putting the prospect on the back burner. Even then, I advise them to restart the effort again (with the same donor)  a few months later.

In fundraising—as in sales—persistence works. You may catch the gatekeeper in a good mood, have some news that the gatekeeper knows the major donor will find interesting, or call one time and the major donor will pick up themselves. Generally speaking, the gatekeeper won’t tell you that the donor doesn’t want to speak with you; they will tell you that the donor is busy or in a meeting, giving you the chance to call back again later.

#2: Build Rapport & Ask the Gatekeeper for Help

If you’re making calls and the gatekeeper is answering (or you’re sending emails and the gatekeeper is responding), but you aren’t able to arrange a time to meet with the donor, try building rapport with the gatekeeper and asking them for help. This means making small talk with the gatekeeper, taking notes about your brief conversations, and remembering things for the next call.

For example, if the assistant mentions that the donor is out of town for a conference, you could reference that the next time you call by saying, “Is Mrs. Jones back from the conference? I hope it went well!”

During your exchanges, ask the gatekeeper for help. Say something like, “I know Mr. Murphy is very busy, Donna. I’ve been trying to get in touch with him for the past month because I know he really cares about poverty in our town, and I would love to talk with him about what we’re doing to help. If you were me, how would you reach out to him? Is there some time that I could call when he will be in?”  You’d be surprised how often gatekeepers will help you eventually get in touch with the donor.

#3: Change Things Up

One of the best strategies for getting around the gatekeeper and reaching your major donor prospect is constantly changing things up. First, be sure to use multiple communication channels: send an email, make a phone call, send a snail mail letter, and reach out over social media. Calls should be at least 50% of your outreach strategy but don’t neglect the other channels.

Second, be sure to change the time of day you call and email. One of the most well-known sales tricks for getting around gatekeepers is calling the prospect outside regular business hours. This means calling early in the morning (before the gatekeeper gets in to work) or late in the evening (after the gatekeeper has left for the day). Generally, the donor will work longer hours than the gatekeeper and may answer their own phone outside of regular business hours.

Of course, you’ll only want to use this strategy when calling the donor’s office. While I advocate using all of the phone numbers at your disposal (including home and cell phone numbers), it would be considered rude to call someone’s home number at 7:30 AM.

#4: Use Lumpy Mail or Send a Letter via FedEx

This is another strategy that is often used in business, and I have seen it work very well in non-profit fundraising.

There are certain types of physical mail that everyone opens and which often get past the gatekeeper. One example is sending a real, paid FedEx envelope. People assume that the contents are important and possibly private (for the recipient only) if you take the time (and spend $10) to send something via FedEx. The same is true for letters sent via certified mail and what I call “lumpy mail.”

Lumpy mail is physical mail that stands out and creates curiosity for the recipient because of what is inside the envelope. Imagine getting a letter in an oversized envelope that includes something lumpy inside… it feels like there’s a small stuffed animal inside (or an action figure or some other “thing”). So long as the letter is clearly from a reputable organization (yours!) and not a crazy person (no return address, no markings saying what is inside), then the person will want to open the letter to see what is in the envelope.

Your best bet when using lumpy mail is to include something small related to your mission. For example, a zoo could include a small stuffed animal, and a school could include an oversized pencil eraser, etc.

Don’t Give Up!

Remember what I said above: you must be persistent when reaching out to a new donor prospect. Don’t give up. Call, email, send letters, and be creative. Finding donors through cold outreach is a numbers game, but you will be far more successful if you reach out often and use the four strategies above to get through the gatekeepers and speak directly to the donors!

Photo by Henning Kesselhut on Unsplash

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